Hydrogen Peroxide → 2-Benzyloxy-5-phenoxyphenol

HRID 892846Notes

Reaction equation

HRID 892846 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][C:10]=1C=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OO.S(=O)(=O)(O)[OH:27]>CO>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][C:10]=1[OH:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 104477522-Benzyloxy-5-phenoxybenzaldehyde

Product 1

HCID 152014472-Benzyloxy-5-phenoxyphenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Benzyloxy-5-phenoxybenzaldehyde (22.25 g, 73 mmol) is dissolved in methanol (200 mL) and treated with hydrogen peroxide (31% in water, 32.0 mL) and concentrated sulfuric acid (15.0 mL). The mixture is stirred overnight at room temperature and evaporated. The residue is dissolved in saturated aqueous sodium chloride solution and extracted with ether. The organic phase is dried over magnesium sulfate and evaporated. Purification of the residue by silica-gel flash chromatography gives 2-benzyloxy-5-phenoxyphenol as a colorless solid.

Workup

  1. customevaporated
  2. dissolutionThe residue is dissolved in saturated aqueous sodium chloride solution
  3. extractionextracted with ether
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. customevaporated
  6. customPurification of the residue by silica-gel flash chromatography

Sources & evidence

ORD record
ord-7f3d9d13f8b94dafb22414c9a40c28e8
Source dataset
uspto-grants-1992_06
Patent number
US05120758

Reaction notes

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